# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ndj-hz-300k
_database_code_depnum_ccdc_archive 'CCDC 2021435'
loop_
_audit_author_name
_audit_author_address
'Youdong Shao'
;Heze University
China
;
_audit_update_record             
;
2020-08-05 deposited with the CCDC.	2020-12-08 downloaded from the CCDC.
;
_audit_creation_date             2020-08-04
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Br N O'
_chemical_formula_sum            'C22 H16 Br N O'
_chemical_formula_weight         390.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   16.7622(2)
_cell_length_b                   7.97140(10)
_cell_length_c                   13.42690(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.2810(10)
_cell_angle_gamma                90
_cell_volume                     1765.27(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8269
_cell_measurement_temperature    300.91(10)
_cell_measurement_theta_max      76.9540
_cell_measurement_theta_min      3.3520
_shelx_estimated_absorpt_T_max   0.738
_shelx_estimated_absorpt_T_min   0.679
_exptl_absorpt_coefficient_mu    3.232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9327
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.197
_diffrn_reflns_theta_min         3.345
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.91(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00   5.00   0.50    0.05    --   46.62 -57.00 -90.00   60
  2  ω    -22.00  18.00   0.50    0.05    --   46.62 -37.00 150.00   80
  3  ω     81.00 117.00   0.50    0.05    --   46.62  37.00-150.00   72
  4  ω    -29.00  18.00   0.50    0.05    --   46.62 -19.00  60.00   94
  5  ω     19.00  46.00   0.50    0.05    --   46.62 -57.00 -90.00   54
  6  ω    -24.00  55.00   0.50    0.05    --   46.62 -57.00  30.00  158
  7  ω    -19.00  23.00   0.50    0.05    --   46.62 -19.00 -90.00   84
  8  ω     35.00  78.00   0.50    0.05    --   46.62  37.00-150.00   86
  9  ω   -105.00 -79.00   0.50    0.18    -- -100.00 125.00-120.00   52
 10  ω   -165.00-136.00   0.50    0.18    -- -100.00 -15.00-180.00   58
 11  ω    -74.00 -28.00   0.50    0.18    -- -100.00  61.00 -60.00   92
 12  ω    -72.00 -29.00   0.50    0.18    -- -100.00  61.00   0.00   86
 13  ω    -54.00 -29.00   0.50    0.18    -- -100.00  45.00-120.00   50
 14  ω   -107.00 -80.00   0.50    0.18    -- -100.00  77.00 -60.00   54
 15  ω   -164.00 -89.00   0.50    0.18    -- -100.00 -61.00  30.00  150
 16  ω    -53.00 -27.00   0.50    0.18    -- -100.00  45.00   0.00   52
 17  ω   -160.00 -87.00   0.50    0.18    -- -100.00 -30.00  90.00  146
 18  ω    -69.00 -32.00   0.50    0.18    -- -100.00 125.00 -90.00   74
 19  ω   -111.00 -77.00   0.50    0.18    -- -100.00 125.00 -90.00   68
 20  ω    -64.00 -39.00   0.50    0.18    -- -100.00 105.00 -22.27   50
 21  ω    -70.00 -45.00   0.50    0.18    -- -100.00  77.00 -60.00   50
 22  ω   -107.00 -67.00   0.50    0.18    -- -100.00 105.00 -22.27   80
 23  ω    -53.00 -28.00   0.50    0.18    -- -100.00  45.00 -90.00   50
 24  ω   -119.00 -83.00   0.50    0.18    -- -100.00 -15.00-180.00   72
 25  ω    -74.00 -38.00   0.50    0.18    -- -100.00  61.00 120.00   72
 26  ω    -74.00 -35.00   0.50    0.18    -- -100.00  61.00-180.00   78
 27  ω    -95.00 -33.00   0.50    0.18    -- -100.00 125.00 -30.00  124
 28  ω     65.00 104.00   0.50    0.18    --  107.75 -94.00  90.00   78
 29  ω     99.00 150.00   0.50    0.18    --  107.75  15.00 -60.00  102
 30  ω     46.00  96.00   0.50    0.18    --  107.75 -94.00 150.00  100
 31  ω     39.00  81.00   0.50    0.18    --  107.75   0.00 150.00   84
 32  ω     35.00  67.00   0.50    0.18    --  107.75 -61.00-180.00   64
 33  ω     38.00  68.00   0.50    0.18    --  107.75 -61.00 150.00   60
 34  ω     84.00 112.00   0.50    0.18    --  107.75-125.00 120.00   56
 35  ω     44.00 110.00   0.50    0.18    --  107.75-125.00  90.00  132
 36  ω     43.00  68.00   0.50    0.18    --  107.75-125.00 120.00   50
 37  ω     70.00 105.00   0.50    0.18    --  107.75 -94.00-180.00   70
 38  ω    125.00 165.00   0.50    0.18    --  107.75   0.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0314767000
_diffrn_orient_matrix_UB_12      0.0302459000
_diffrn_orient_matrix_UB_13      0.1135296000
_diffrn_orient_matrix_UB_21      -0.0272628000
_diffrn_orient_matrix_UB_22      -0.1778246000
_diffrn_orient_matrix_UB_23      0.0238702000
_diffrn_orient_matrix_UB_31      0.0836032000
_diffrn_orient_matrix_UB_32      -0.0693879000
_diffrn_orient_matrix_UB_33      -0.0117673000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                3355
_reflns_number_total             3420
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.035(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+0.7448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0676
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.035(19)
 -0.035(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84596(2) 0.21918(6) 0.18810(3) 0.06338(13) Uani 1 1 d . . . . .
O1 O 0.87986(15) 0.7822(3) 0.38646(18) 0.0489(5) Uani 1 1 d . . . . .
H1 H 0.851686 0.816047 0.426326 0.073 Uiso 1 1 calc R U . . .
N1 N 0.69267(14) 0.4180(3) 0.45058(17) 0.0365(5) Uani 1 1 d . . . . .
C1 C 0.64539(15) 0.4249(4) 0.3567(2) 0.0359(5) Uani 1 1 d . . . . .
C2 C 0.81947(17) 0.4439(4) 0.5634(2) 0.0384(6) Uani 1 1 d . . . . .
C3 C 0.51300(17) 0.3839(4) 0.2545(2) 0.0483(7) Uani 1 1 d . . . . .
H3 H 0.458582 0.355353 0.248925 0.058 Uiso 1 1 calc R U . . .
C4 C 0.67639(16) 0.4695(4) 0.2689(2) 0.0362(6) Uani 1 1 d . . . . .
C5 C 0.56191(17) 0.3828(4) 0.3471(2) 0.0432(6) Uani 1 1 d . . . . .
H5 H 0.540657 0.354536 0.404241 0.052 Uiso 1 1 calc R U . . .
C6 C 0.79559(15) 0.5617(4) 0.19139(19) 0.0374(5) Uani 1 1 d . . . . .
C7 C 0.75965(15) 0.5167(3) 0.28195(19) 0.0346(5) Uani 1 1 d . . . . .
C8 C 0.8891(2) 0.3448(4) 0.5784(3) 0.0537(8) Uani 1 1 d . . . . .
H8 H 0.904247 0.288531 0.524080 0.064 Uiso 1 1 calc R U . . .
C9 C 0.83538(17) 0.4439(4) 0.1415(2) 0.0435(6) Uani 1 1 d . . . . .
C10 C 0.88824(17) 0.6054(4) 0.3951(2) 0.0411(6) Uani 1 1 d . . . . .
H10A H 0.917408 0.576871 0.462030 0.049 Uiso 1 1 calc R U . . .
H10B H 0.919330 0.564531 0.345737 0.049 Uiso 1 1 calc R U . . .
C11 C 0.80549(15) 0.5218(3) 0.37775(19) 0.0354(5) Uani 1 1 d . . . . .
C12 C 0.54377(18) 0.4275(5) 0.1676(2) 0.0498(7) Uani 1 1 d . . . . .
H12 H 0.509575 0.427616 0.104951 0.060 Uiso 1 1 calc R U . . .
C13 C 0.76980(16) 0.4628(3) 0.46006(19) 0.0355(5) Uani 1 1 d . . . . .
C14 C 0.62359(18) 0.4699(4) 0.1741(2) 0.0439(7) Uani 1 1 d . . . . .
H14 H 0.643248 0.499042 0.115915 0.053 Uiso 1 1 calc R U . . .
C15 C 0.78988(16) 0.7254(6) 0.1532(2) 0.0479(6) Uani 1 1 d . . . . .
H15 H 0.763268 0.807021 0.184480 0.057 Uiso 1 1 calc R U . . .
C16 C 0.9357(2) 0.3300(5) 0.6743(3) 0.0678(11) Uani 1 1 d . . . . .
H16 H 0.981774 0.262702 0.684305 0.081 Uiso 1 1 calc R U . . .
C17 C 0.7971(2) 0.5245(4) 0.6454(2) 0.0474(7) Uani 1 1 d . . . . .
H17 H 0.749929 0.588344 0.636655 0.057 Uiso 1 1 calc R U . . .
C18 C 0.8233(2) 0.7674(5) 0.0696(2) 0.0556(8) Uani 1 1 d . . . . .
H18 H 0.818769 0.876694 0.045060 0.067 Uiso 1 1 calc R U . . .
C19 C 0.8633(2) 0.6491(5) 0.0223(2) 0.0585(9) Uani 1 1 d . . . . .
H19 H 0.886033 0.678675 -0.033517 0.070 Uiso 1 1 calc R U . . .
C20 C 0.8696(2) 0.4869(5) 0.0580(2) 0.0567(8) Uani 1 1 d . . . . .
H20 H 0.896585 0.406444 0.026449 0.068 Uiso 1 1 calc R U . . .
C21 C 0.8448(3) 0.5102(6) 0.7407(3) 0.0619(10) Uani 1 1 d . . . . .
H21 H 0.829851 0.565590 0.795561 0.074 Uiso 1 1 calc R U . . .
C22 C 0.9139(3) 0.4147(6) 0.7543(3) 0.0710(11) Uani 1 1 d . . . . .
H22 H 0.946260 0.407263 0.818100 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.895(3) . ?
O1 H1 0.8200 . ?
O1 C10 1.419(4) . ?
N1 C1 1.366(3) . ?
N1 C13 1.325(4) . ?
C1 C4 1.415(4) . ?
C1 C5 1.422(4) . ?
C2 C8 1.393(5) . ?
C2 C13 1.493(4) . ?
C2 C17 1.383(4) . ?
C3 H3 0.9300 . ?
C3 C5 1.361(4) . ?
C3 C12 1.401(4) . ?
C4 C7 1.426(4) . ?
C4 C14 1.415(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.494(3) . ?
C6 C9 1.391(4) . ?
C6 C15 1.400(5) . ?
C7 C11 1.376(4) . ?
C8 H8 0.9300 . ?
C8 C16 1.386(5) . ?
C9 C20 1.389(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.519(4) . ?
C11 C13 1.427(3) . ?
C12 H12 0.9300 . ?
C12 C14 1.368(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C18 1.383(4) . ?
C16 H16 0.9300 . ?
C16 C22 1.373(7) . ?
C17 H17 0.9300 . ?
C17 C21 1.387(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.372(7) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 H1 109.5 . . ?
C13 N1 C1 118.3(2) . . ?
N1 C1 C4 122.7(2) . . ?
N1 C1 C5 118.3(2) . . ?
C4 C1 C5 119.0(3) . . ?
C8 C2 C13 120.4(3) . . ?
C17 C2 C8 119.1(3) . . ?
C17 C2 C13 120.5(3) . . ?
C5 C3 H3 119.7 . . ?
C5 C3 C12 120.7(3) . . ?
C12 C3 H3 119.7 . . ?
C1 C4 C7 117.5(2) . . ?
C14 C4 C1 119.1(2) . . ?
C14 C4 C7 123.5(2) . . ?
C1 C5 H5 119.9 . . ?
C3 C5 C1 120.3(3) . . ?
C3 C5 H5 119.9 . . ?
C9 C6 C7 121.9(3) . . ?
C9 C6 C15 117.4(2) . . ?
C15 C6 C7 120.7(2) . . ?
C4 C7 C6 119.4(2) . . ?
C11 C7 C4 119.6(2) . . ?
C11 C7 C6 121.0(2) . . ?
C2 C8 H8 119.9 . . ?
C16 C8 C2 120.1(4) . . ?
C16 C8 H8 119.9 . . ?
C6 C9 Br1 120.2(2) . . ?
C20 C9 Br1 118.2(3) . . ?
C20 C9 C6 121.6(3) . . ?
O1 C10 H10A 109.6 . . ?
O1 C10 H10B 109.6 . . ?
O1 C10 C11 110.4(3) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C7 C11 C10 119.9(2) . . ?
C7 C11 C13 118.2(2) . . ?
C13 C11 C10 121.6(2) . . ?
C3 C12 H12 119.7 . . ?
C14 C12 C3 120.7(3) . . ?
C14 C12 H12 119.7 . . ?
N1 C13 C2 115.8(2) . . ?
N1 C13 C11 123.4(2) . . ?
C11 C13 C2 120.8(2) . . ?
C4 C14 H14 119.9 . . ?
C12 C14 C4 120.3(3) . . ?
C12 C14 H14 119.9 . . ?
C6 C15 H15 119.6 . . ?
C18 C15 C6 120.8(3) . . ?
C18 C15 H15 119.6 . . ?
C8 C16 H16 120.0 . . ?
C22 C16 C8 120.0(4) . . ?
C22 C16 H16 120.0 . . ?
C2 C17 H17 119.9 . . ?
C2 C17 C21 120.2(3) . . ?
C21 C17 H17 119.9 . . ?
C15 C18 H18 119.6 . . ?
C19 C18 C15 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C9 C20 H20 120.1 . . ?
C19 C20 C9 119.7(3) . . ?
C19 C20 H20 120.1 . . ?
C17 C21 H21 119.9 . . ?
C22 C21 C17 120.1(4) . . ?
C22 C21 H21 119.9 . . ?
C16 C22 H22 119.8 . . ?
C21 C22 C16 120.4(3) . . ?
C21 C22 H22 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C9 C20 C19 -179.8(3) . . . . ?
O1 C10 C11 C7 72.0(3) . . . . ?
O1 C10 C11 C13 -101.5(3) . . . . ?
N1 C1 C4 C7 -3.1(4) . . . . ?
N1 C1 C4 C14 178.6(3) . . . . ?
N1 C1 C5 C3 -178.4(3) . . . . ?
C1 N1 C13 C2 -176.8(3) . . . . ?
C1 N1 C13 C11 1.6(4) . . . . ?
C1 C4 C7 C6 178.8(3) . . . . ?
C1 C4 C7 C11 -1.9(4) . . . . ?
C1 C4 C14 C12 0.0(5) . . . . ?
C2 C8 C16 C22 -0.8(6) . . . . ?
C2 C17 C21 C22 -0.7(5) . . . . ?
C3 C12 C14 C4 0.3(5) . . . . ?
C4 C1 C5 C3 0.7(5) . . . . ?
C4 C7 C11 C10 -167.4(3) . . . . ?
C4 C7 C11 C13 6.3(4) . . . . ?
C5 C1 C4 C7 177.8(3) . . . . ?
C5 C1 C4 C14 -0.5(4) . . . . ?
C5 C3 C12 C14 0.0(5) . . . . ?
C6 C7 C11 C10 12.0(4) . . . . ?
C6 C7 C11 C13 -174.4(3) . . . . ?
C6 C9 C20 C19 -0.9(5) . . . . ?
C6 C15 C18 C19 -0.3(5) . . . . ?
C7 C4 C14 C12 -178.2(3) . . . . ?
C7 C6 C9 Br1 -0.4(3) . . . . ?
C7 C6 C9 C20 -179.2(3) . . . . ?
C7 C6 C15 C18 179.8(3) . . . . ?
C7 C11 C13 N1 -6.5(4) . . . . ?
C7 C11 C13 C2 171.9(2) . . . . ?
C8 C2 C13 N1 122.6(3) . . . . ?
C8 C2 C13 C11 -55.9(4) . . . . ?
C8 C2 C17 C21 1.8(5) . . . . ?
C8 C16 C22 C21 2.0(6) . . . . ?
C9 C6 C7 C4 -93.6(3) . . . . ?
C9 C6 C7 C11 87.1(3) . . . . ?
C9 C6 C15 C18 -0.5(4) . . . . ?
C10 C11 C13 N1 167.1(3) . . . . ?
C10 C11 C13 C2 -14.5(4) . . . . ?
C12 C3 C5 C1 -0.5(5) . . . . ?
C13 N1 C1 C4 3.2(4) . . . . ?
C13 N1 C1 C5 -177.7(3) . . . . ?
C13 C2 C8 C16 178.9(3) . . . . ?
C13 C2 C17 C21 -178.1(3) . . . . ?
C14 C4 C7 C6 -3.0(4) . . . . ?
C14 C4 C7 C11 176.3(3) . . . . ?
C15 C6 C7 C4 86.1(3) . . . . ?
C15 C6 C7 C11 -93.3(3) . . . . ?
C15 C6 C9 Br1 179.9(2) . . . . ?
C15 C6 C9 C20 1.2(4) . . . . ?
C15 C18 C19 C20 0.5(5) . . . . ?
C17 C2 C8 C16 -1.1(5) . . . . ?
C17 C2 C13 N1 -57.4(4) . . . . ?
C17 C2 C13 C11 124.1(3) . . . . ?
C17 C21 C22 C16 -1.2(6) . . . . ?
C18 C19 C20 C9 0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.599
_oxdiff_exptl_absorpt_empirical_full_min 0.701
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.035(19)
2 -0.035(19)

